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Hydrochloric Acid → 2-(1-(4-Cyanophenyl)-4-piperidyl)ethanoic acid

HRID 1004517
Notes
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Reaction equation

HRID 1004517 reaction equation
C([O:3][C:4](=[O:20])[CH2:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]#[N:19])=[CH:14][CH:13]=2)[CH2:8][CH2:7]1)C.[OH-].[Na+].Cl>CO.C1COCC1>[C:18]([C:15]1[CH:14]=[CH:13][C:12]([N:9]2[CH2:8][CH2:7][CH:6]([CH2:5][C:4]([OH:20])=[O:3])[CH2:11][CH2:10]2)=[CH:17][CH:16]=1)#[N:19]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 54529684HCID 54529684, compound

Product 1

HCID 187940782-(1-(4-Cyanophenyl)-4-piperidyl)ethanoic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028Tetrahydrofuran
Solvent

Procedure

The compound (1.38 g) obtained in the above (2) is dissolved in a mixture of methanol (20 ml) and THF (10 ml), and thereto is added an aqueous sodium hydroxide solution (NaOH; 2.1 g, water; 10 ml), and the mixture is stirred at room temperature for 30 minutes. The pH value of the mixture is adjusted to pH 1 with conc. hydrochloric acid, and the reaction mixture is concentrated under reduced pressure. To the residue is added isopropanol, and the mixture is stirred at room temperature for one hour, and the precipitates are removed by filtration. The filtrate is concentrated under reduced pressure to give the title compound (1.20 g) as a powder.

Workup

  1. concentrationthe reaction mixture is concentrated under reduced pressure
  2. additionTo the residue is added isopropanol
  3. stirringthe mixture is stirred at room temperature for one hour
  4. customthe precipitates are removed by filtration
  5. concentrationThe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-cd44082377c0483fa7a36204cccb97f9
Source dataset
uspto-grants-2000_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06048854

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes